Enantioselective Construction of Bispirooxindoles via Squaramide‐Catalysed Cascade Michael/Cyclization Reaction

A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have been successfully applied to develop a bifunctional squaramide‐catalyzed cascade Michael/cyclization reaction strategy. Various cyclopentene‐b...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 361; no. 14; pp. 3387 - 3393
Main Authors Zhao, Bo‐Liang, Lin, Ye, Du, Da‐Ming
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 11.07.2019
Wiley Subscription Services, Inc
Subjects
Bispirooxindoles
Cascade reaction
Catalysis
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Cyclopentene
Enantiomers
Michael/cyclization
Organocatalysis
Physical Sciences
Science & Technology
Squaramides
Cascade reaction
3+2 ANNULATION
Bispirooxindoles
ASYMMETRIC-SYNTHESIS
Michael/cyclization
Squaramides
Organocatalysis
CYCLIZATION
SPIROOXINDOLES
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Summary:A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have been successfully applied to develop a bifunctional squaramide‐catalyzed cascade Michael/cyclization reaction strategy. Various cyclopentene‐bispirooxindoles with three continuous stereocenters, two of which are quaternary spiro‐stereocenters, were constructed in good yields with excellent stereoselectivities (up to >20:1 dr, >99% ee).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900358